EP0754674A4 - Novel carboxylic ester derivatives, process for producing the same, and insecticide or insectifuge containing the same - Google Patents

Novel carboxylic ester derivatives, process for producing the same, and insecticide or insectifuge containing the same

Info

Publication number
EP0754674A4
EP0754674A4 EP96901950A EP96901950A EP0754674A4 EP 0754674 A4 EP0754674 A4 EP 0754674A4 EP 96901950 A EP96901950 A EP 96901950A EP 96901950 A EP96901950 A EP 96901950A EP 0754674 A4 EP0754674 A4 EP 0754674A4
Authority
EP
European Patent Office
Prior art keywords
group
same
insecticides
hydrogen atom
proofing agents
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP96901950A
Other languages
German (de)
French (fr)
Other versions
EP0754674B1 (en
EP0754674A1 (en
Inventor
Yoshio Katsuda
Koji Nakayama
Yoshihiro Minamite
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dainihon Jochugiku Co Ltd
Original Assignee
Dainihon Jochugiku Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dainihon Jochugiku Co Ltd filed Critical Dainihon Jochugiku Co Ltd
Publication of EP0754674A1 publication Critical patent/EP0754674A1/en
Publication of EP0754674A4 publication Critical patent/EP0754674A4/en
Application granted granted Critical
Publication of EP0754674B1 publication Critical patent/EP0754674B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/743—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a three-membered ring and with unsaturation outside the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/54—Radicals substituted by oxygen atoms

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The derivatives of esters of carboxylic acids represented by the general formula I: <CHEM> wherein: R1 is an alkyl group having a chain or branched chain of 1 to 4 carbon atoms; and R2 is a group represented by the following general formulae II, III or IV; <CHEM> wherein: R3 is a hydrogen atom or a methyl group; X is an oxygen atom or a methylidene group; R4 is an hydrogen atom or an ethynyl group; R5 and R6 are alike or differently selected from the group consisting of hydrogen, fluorine, chlorine atoms or methyl group; R7 is a hydrogen atom or a trifluoromethyl group; R8 is selected from the group consisting of propargyl, methoxymethyl or methylthio groups; or R7 and R8 may combine with each other to form a methylenedioxy chain; and the process for manufacturing the same, and the insecticides and the insect proofing agents containing the same as an active ingredient. The compounds represented by the general formula I are useful ingredients of insecticides and insect proofing agents which have both a fast-acting property and a lethal effect, and moreover, are highly safe to mammals; and therefore, insecticides and insect proofing agents containing the above compounds have a highly practical use.
EP96901950A 1995-02-07 1996-02-07 Novel carboxylic ester derivatives, process for producing the same, and insecticide or insectifuge containing the same Expired - Lifetime EP0754674B1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP54936/95 1995-02-07
JP5493695 1995-02-07
JP5493695 1995-02-07
PCT/JP1996/000254 WO1996024573A1 (en) 1995-02-07 1996-02-07 Novel carboxylic ester derivatives, process for producing the same, and insecticide or insectifuge containing the same

Publications (3)

Publication Number Publication Date
EP0754674A1 EP0754674A1 (en) 1997-01-22
EP0754674A4 true EP0754674A4 (en) 1998-07-08
EP0754674B1 EP0754674B1 (en) 2001-12-19

Family

ID=12984527

Family Applications (1)

Application Number Title Priority Date Filing Date
EP96901950A Expired - Lifetime EP0754674B1 (en) 1995-02-07 1996-02-07 Novel carboxylic ester derivatives, process for producing the same, and insecticide or insectifuge containing the same

Country Status (24)

Country Link
US (1) US6107339A (en)
EP (1) EP0754674B1 (en)
JP (1) JP3376395B2 (en)
CN (1) CN1138752C (en)
AT (1) ATE211127T1 (en)
AU (1) AU692992B2 (en)
BG (1) BG63199B1 (en)
BR (1) BR9605109A (en)
CA (1) CA2187277C (en)
CZ (1) CZ290887B6 (en)
DE (1) DE69618096T2 (en)
FI (1) FI963943A (en)
HU (1) HU216081B (en)
MY (1) MY114703A (en)
NO (1) NO306942B1 (en)
OA (1) OA10590A (en)
PL (1) PL182472B1 (en)
RO (1) RO118424B1 (en)
RU (1) RU2168492C2 (en)
SI (1) SI9620006B (en)
SK (1) SK284829B6 (en)
TW (1) TW342384B (en)
UA (1) UA57591C2 (en)
WO (1) WO1996024573A1 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4474745B2 (en) * 1999-12-10 2010-06-09 住友化学株式会社 Ester compound, its use and production intermediate
WO2003031388A1 (en) * 2000-06-12 2003-04-17 Dainihon Jochugiku Co., Ltd Propargylbenzyl alcohol ester derivative, process for producing the same, and insecticide/insectifuge containing the same
DE10320505A1 (en) * 2003-05-08 2004-11-25 Bayer Healthcare Ag Means for controlling parasites on animals
ZA200409433B (en) * 2003-11-26 2005-07-14 Sumitomo Chemical Co Process for the preparation of carboxylic acid esters.
CN102020564A (en) * 2009-09-17 2011-04-20 上海生农生化制品有限公司 Fluoro-containing cyclopropane carboxylate with acetylenic bond and preparation method and use thereof

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2458656A (en) * 1946-03-26 1949-01-11 Thompson Boyce Plant Res Esters of piperonyl chrysanthemum carboxylic acid
US2886485A (en) * 1957-09-12 1959-05-12 William F Barthel 6-bromopiperonyl and 6-chloropiperonyl esters of chrysanthemumic acid as insecticides
DE1793312A1 (en) * 1968-08-29 1971-07-08 Basf Ag Substituted chrysanthemum acid esters and pest repellants containing them
JPS49489B1 (en) * 1970-06-13 1974-01-08
US4024163A (en) * 1972-05-25 1977-05-17 National Research Development Corporation Insecticides
US4370346A (en) * 1979-12-21 1983-01-25 Imperial Chemical Industries Plc Halogenated esters
GB2066810A (en) * 1979-12-21 1981-07-15 Ici Ltd Fluorinated benzyl esters of cyclopropane carboxylic acids
FR2482955A1 (en) * 1980-05-23 1981-11-27 Roussel Uclaf NOVEL DERIVATIVES OF CYCLOPROPANE CARBOXYLIC ACID, PROCESS FOR PREPARING THEM AND THEIR APPLICATION TO THE FIGHT AGAINST PARASITES
FR2536392A2 (en) * 1982-11-22 1984-05-25 Roussel Uclaf New cyclopropanecarboxylic acid derivatives, process for their preparation and their application to the fight against parasites.
US4489093A (en) * 1980-10-01 1984-12-18 Roussel Uclaf Insecticidal esters
FR2526422B1 (en) * 1982-05-06 1985-09-20 Roussel Uclaf NOVEL PROCESS FOR THE PREPARATION OF DERIVATIVES OF CYCLOPROPANE CARBOXYLIC ACID
US4542142A (en) * 1982-11-22 1985-09-17 Roussel Uclaf Insecticidal cyclopropane carboxylic acid derivatives with 3-unsaturated-side chain
FR2536748A1 (en) * 1982-11-25 1984-06-01 Roussel Uclaf NOVEL ESTERS DERIVED FROM 2,2-DIMETHYL CYCLOPROPANE CARBOXYLIC ACIDS AND BIARYLIC ALCOHOLS, PROCESS FOR PREPARING THEM AND THEIR APPLICATION TO THE FIGHT AGAINST PARASITES
FR2539411B2 (en) * 1983-01-17 1986-04-25 Roussel Uclaf NOVEL DERIVATIVES OF CYCLOPROPANE CARBOXYLIC ACID, THEIR PREPARATION METHOD, THEIR APPLICATION TO THE CONTROL OF PESTS
FR2610624B1 (en) * 1987-02-06 1989-06-09 Roussel Uclaf NOVEL ESTERS OF PYRETHRIC ACID-LIKE CYCLOPROPANECARBOXYLIC ACIDS, THEIR PREPARATION PROCESS AND THEIR APPLICATION TO PEST CONTROL
JPS63267706A (en) * 1987-04-22 1988-11-04 Dainippon Jiyochiyuugiku Kk Insecticide containing benzyl alcohol ester for smoking combustion and thermal evaporation and production thereof
JP2570388B2 (en) * 1988-06-10 1997-01-08 住友化学工業株式会社 Carboxylic acid esters and their use as insecticides
FR2687152A1 (en) * 1992-02-07 1993-08-13 Roussel Uclaf NOVEL PYRETHRINOUID ESTERS DERIVED FROM FURANIC OR THIOPHENIC ALCOHOL, PROCESS FOR THEIR PREPARATION AND THEIR USE AS PESTICIDES
FR2687666A1 (en) * 1992-02-21 1993-08-27 Roussel Uclaf NOVEL PYRETHRINOUS ESTERS DERIVED FROM 6- (TRIFLUOROMETHYL) BENZYL ALCOHOL, PROCESS FOR THEIR PREPARATION AND THEIR USE AS PESTICIDES
JP3063871B2 (en) * 1992-03-30 2000-07-12 大日本除蟲菊株式会社 Insecticides, insect repellents and repellents containing substituted benzyl alcohol ester derivatives, and insecticidal, insect repellent and repellent methods using the same.
FR2691966A1 (en) * 1992-06-04 1993-12-03 Roussel Uclaf Novel process for the preparation of 2,2-dimethyl-3 - [(z) 1-propenyl] cyclopropane carboxylic acid esters and intermediates
JPH07112947A (en) * 1993-08-24 1995-05-02 Sumitomo Chem Co Ltd Ester compound, harmful organism controlling agent containing the compound as active component, production intermediate therefor and its production

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
No further relevant documents disclosed *

Also Published As

Publication number Publication date
CA2187277C (en) 2002-04-30
CZ290887B6 (en) 2002-11-13
HUP9603080A2 (en) 1997-05-28
HUP9603080A3 (en) 1997-08-28
DE69618096D1 (en) 2002-01-31
SK284829B6 (en) 2005-12-01
EP0754674B1 (en) 2001-12-19
CN1138752C (en) 2004-02-18
SI9620006B (en) 2001-12-31
RU2168492C2 (en) 2001-06-10
BG63199B1 (en) 2001-06-29
NO964219L (en) 1996-11-07
RO118424B1 (en) 2003-05-30
SK139796A3 (en) 1997-04-09
FI963943A0 (en) 1996-10-02
CZ325996A3 (en) 1997-04-16
CN1148379A (en) 1997-04-23
EP0754674A1 (en) 1997-01-22
WO1996024573A1 (en) 1996-08-15
NO964219D0 (en) 1996-10-04
PL182472B1 (en) 2002-01-31
AU692992B2 (en) 1998-06-18
ATE211127T1 (en) 2002-01-15
BG100966A (en) 1998-03-31
CA2187277A1 (en) 1996-08-15
MY114703A (en) 2002-12-31
PL316872A1 (en) 1997-02-17
BR9605109A (en) 1997-10-07
NO306942B1 (en) 2000-01-17
JP3376395B2 (en) 2003-02-10
FI963943A (en) 1996-10-16
UA57591C2 (en) 2003-06-16
US6107339A (en) 2000-08-22
SI9620006A (en) 1997-04-30
OA10590A (en) 2002-07-15
DE69618096T2 (en) 2002-07-18
TW342384B (en) 1998-10-11
AU4632596A (en) 1996-08-27
HU216081B (en) 1999-04-28

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